Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues
N-(Substituted)-5-(1-(4-methoxyphenylsulfonyl)piperidin-4-yl)-4H-1,2,4-triazol-3-ylthio) acetamide were synthesized by following conventional as well as microwave assisted protocol through five consecutive steps under the impact of various reaction conditions to control the reaction time and the yie...
| Published in: | Pakistan journal of pharmaceutical sciences |
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| Format: | Article |
| Language: | English |
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NLM (Medline)
2018
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| Online Access: | https://www.scopus.com/inward/record.uri?eid=2-s2.0-85064722727&partnerID=40&md5=0a69ac8f82ce083cf95b3c710152cca8 |
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2-s2.0-85064722727 Virk N.A.; Rehman A.; Abbasi M.A.; Siddiqui S.Z.; Rashid U.; Iqbal J.; Saleem M.; Ashraf M.; Shahid W.; Shah S.A.A. Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues 2018 Pakistan journal of pharmaceutical sciences 31 4 https://www.scopus.com/inward/record.uri?eid=2-s2.0-85064722727&partnerID=40&md5=0a69ac8f82ce083cf95b3c710152cca8 N-(Substituted)-5-(1-(4-methoxyphenylsulfonyl)piperidin-4-yl)-4H-1,2,4-triazol-3-ylthio) acetamide were synthesized by following conventional as well as microwave assisted protocol through five consecutive steps under the impact of various reaction conditions to control the reaction time and the yield of product. Starting from 4-methoxybenzenesulfonyl chloride and ethyl isonipecotate, product 3 was obtained which was converted into product 4 by treating with hydrazine hydrate. In step 3, the product 4 was refluxed with methyl isothiocyanate and KOH to yield compound 5 which was finally treated with variety of N-substituted acetamides to yield an array of different new compounds (8a-k). These synthesized compounds were evaluated for their inhibition potential against bovine carbonic anhydrase (bCA-II), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Compound 8g demonstrated good activity against bCA-II, AChE and BChE with IC50 values of 8.69 ± 0.38 μM, 11.87±0.19 μM and 26.01±0.55 μM respectively. SAR studies assisted with molecular docking were carried out to explore the mode of binding of the compounds against the studied enzymes. NLM (Medline) 1011601X English Article |
| author |
Virk N.A.; Rehman A.; Abbasi M.A.; Siddiqui S.Z.; Rashid U.; Iqbal J.; Saleem M.; Ashraf M.; Shahid W.; Shah S.A.A. |
| spellingShingle |
Virk N.A.; Rehman A.; Abbasi M.A.; Siddiqui S.Z.; Rashid U.; Iqbal J.; Saleem M.; Ashraf M.; Shahid W.; Shah S.A.A. Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues |
| author_facet |
Virk N.A.; Rehman A.; Abbasi M.A.; Siddiqui S.Z.; Rashid U.; Iqbal J.; Saleem M.; Ashraf M.; Shahid W.; Shah S.A.A. |
| author_sort |
Virk N.A.; Rehman A.; Abbasi M.A.; Siddiqui S.Z.; Rashid U.; Iqbal J.; Saleem M.; Ashraf M.; Shahid W.; Shah S.A.A. |
| title |
Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues |
| title_short |
Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues |
| title_full |
Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues |
| title_fullStr |
Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues |
| title_full_unstemmed |
Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues |
| title_sort |
Conventional versus microwave assisted synthesis, molecular docking and enzyme inhibitory activities of new 3,4,5-trisubstituted-1,2,4-triazole analogues |
| publishDate |
2018 |
| container_title |
Pakistan journal of pharmaceutical sciences |
| container_volume |
31 |
| container_issue |
4 |
| doi_str_mv |
|
| url |
https://www.scopus.com/inward/record.uri?eid=2-s2.0-85064722727&partnerID=40&md5=0a69ac8f82ce083cf95b3c710152cca8 |
| description |
N-(Substituted)-5-(1-(4-methoxyphenylsulfonyl)piperidin-4-yl)-4H-1,2,4-triazol-3-ylthio) acetamide were synthesized by following conventional as well as microwave assisted protocol through five consecutive steps under the impact of various reaction conditions to control the reaction time and the yield of product. Starting from 4-methoxybenzenesulfonyl chloride and ethyl isonipecotate, product 3 was obtained which was converted into product 4 by treating with hydrazine hydrate. In step 3, the product 4 was refluxed with methyl isothiocyanate and KOH to yield compound 5 which was finally treated with variety of N-substituted acetamides to yield an array of different new compounds (8a-k). These synthesized compounds were evaluated for their inhibition potential against bovine carbonic anhydrase (bCA-II), acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) enzymes. Compound 8g demonstrated good activity against bCA-II, AChE and BChE with IC50 values of 8.69 ± 0.38 μM, 11.87±0.19 μM and 26.01±0.55 μM respectively. SAR studies assisted with molecular docking were carried out to explore the mode of binding of the compounds against the studied enzymes. |
| publisher |
NLM (Medline) |
| issn |
1011601X |
| language |
English |
| format |
Article |
| accesstype |
|
| record_format |
scopus |
| collection |
Scopus |
| _version_ |
1809678483182321664 |